From Organic Chemistry - Department of Chemistry
(4,5,9,11,12/98)(1,9,10/99)
Neuman
Chapter 1
Chapter 1
Organic Molecules and Chemical Bonding
from
Organic Chemistry
by
Robert C. Neuman, Jr.
Professor of Chemistry, emeritus
University of California, Riverside
orgchembyneuman@
Chapter Outline of the Book
**************************************************************************************
I. Foundations
1.
Organic Molecules and Chemical Bonding
2.
Alkanes and Cycloalkanes
3.
Haloalkanes, Alcohols, Ethers, and Amines
4.
Stereochemistry
5.
Organic Spectrometry
II. Reactions, Mechanisms, Multiple Bonds
6.
Organic Reactions *(Not yet Posted)
7.
Reactions of Haloalkanes, Alcohols, and Amines. Nucleophilic Substitution
8.
Alkenes and Alkynes
9.
Formation of Alkenes and Alkynes. Elimination Reactions
10.
Alkenes and Alkynes. Addition Reactions
11.
Free Radical Addition and Substitution Reactions
III. Conjugation, Electronic Effects, Carbonyl Groups
12.
Conjugated and Aromatic Molecules
13.
Carbonyl Compounds. Ketones, Aldehydes, and Carboxylic Acids
14.
Substituent Effects
15.
Carbonyl Compounds. Esters, Amides, and Related Molecules
IV. Carbonyl and Pericyclic Reactions and Mechanisms
16.
Carbonyl Compounds. Addition and Substitution Reactions
17.
Oxidation and Reduction Reactions
18.
Reactions of Enolate Ions and Enols
19.
Cyclization and Pericyclic Reactions *(Not yet Posted)
V. Bioorganic Compounds
20.
Carbohydrates
21.
Lipids
22.
Peptides, Proteins, and ¦Á?Amino Acids
23.
Nucleic Acids
**************************************************************************************
*Note: Chapters marked with an (*) are not yet posted.
0
(4,5,9,11,12/98)(1,9,10/99)
1:
Neuman
Chapter 1
Organic Molecules and Chemical Bonding
Preview
1-3
1.1 Organic Molecules
1-4
1-4
Bonding Characteristics of Atoms (1.1A)
Bonds and Unshared Electron Pairs for C, N, O, and F
Bonds and Unshared Electron Pairs for Other Atoms
Structures of Organic Molecules
Compounds with Four Single Bonds to C (1.1B)
Alkanes (C-C and C-H Bonds)
Compounds with C-X, C-O, or C-N Bonds
Additional R Groups on N or O
Functional Groups
Compounds with Double and Triple Bonds to C (1.1C)
Alkenes (C=C) and Alkynes (C¡ÔC)
Compounds with C=N, C¡ÔN, and C=O Bonds
Functional Group Summary
Compounds With C=O Bonded to N, O, or X (1.1D)
An Overview of Organic Functional Groups (1.1E)
1.2 Chemical Bonds
1-8
1-12
1-19
1-19
1-24
Localized Molecular Orbitals (1.2A)
Electronic Structure of Atoms (1.2B)
Electron Configurations
Atomic Orbitals
Lobes and Nodes
Chemical Bonds in Alkanes (1.2C)
C-H Bonds in CH4
sp3 Hybrid Orbitals of C
C-H and C-C Bonds in Ethane
C-H and C-C Molecular Orbitals
Chemical Bonds in Alkenes and Alkynes (1.2D)
Hybridization of C in C=C Bonds
C-H and C=C Molecular Orbitals
Hybridization of C in C¡ÔC Bonds
The Shapes of Molecules (VSEPR) (1.2E)
(continued next page)
1
1-26
1-29
1-36
1-44
1-24
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Neuman
Chapter 1
1.2 Chemical Bonds (continued)
Bonds between C and N, O, or X (1.2F)
Carbon-Nitrogen Bonds
CH3-NH2 (sp3 N)
CH2=NH (sp2 N)
1-44
H-C¡ÔN (sp N)
Carbon-Oxygen Bonds
Carbon-Halogen Bonds
1.3 Organic Chemistry
1-51
1-53
1-54
1-54
Molecular Structure (1.3A)
Chemical Reactions (1.3B)
Bioorganic Chemistry (1.3C)
1.4 Bon Voyage!
1-55
2
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1:
Neuman
Chapter 1
Organic Molecules and Chemical Bonding
?Organic Molecules
?Chemical Bonds
?Organic Chemistry
?Bon voyage
Preview
Organic chemistry describes the structures, properties, preparation, and reactions of a vast
array of molecules that we call organic compounds. There are many different types of
organic compounds, but all have carbon as their principal constituent atom. These carbon
atoms form a carbon skeleton or carbon backbone that has other bonded atoms such as H,
N, O, S, and the halogens (F, Cl, Br, and I).
We frequently hear the term "organic" in everyday language where it describes or refers to
substances that are "natural". This is probably a result of the notion of early scientists that all
organic compounds came from living systems and possessed a "vital force". However,
chemists learned over 170 years ago that this is not the case. Organic compounds are major
components of living systems, but chemists can make many of them in the laboratory from
substances that have no direct connection with living systems. Chemically speaking, a pure
sample of an organic compound such as Vitamin C prepared in a laboratory is chemically
identical to a pure sample of Vitamin C isolated from a natural source such as an orange or
other citrus fruit.
Your journey through organic chemistry will be challenging because of the large amount of
information that you will need to learn and understand. However, we will explore this
subject in a systematic manner so that it is not a vast collection of isolated facts. What you
learn in one chapter will serve as building blocks for the material in the chapter that follows
it. In this sense, you may find that organic chemistry is different from general chemistry.
That course consists of a variety of discrete topics usually divided into separate segments in
textbooks. In contrast, your organic chemistry instructors will present a course in which each
new topic uses information from previous topics to raise your understanding of organic
chemistry to successively higher levels.
This chapter provides a foundation for your studies of organic chemistry. It begins with an
introduction to the important classes of organic molecules followed by a description of
3
(4,5,9,11,12/98)(1,9,10/99)
Neuman
Chapter 1
chemical bonding in those molecules. It concludes with a brief survey of the various topics
in organic chemistry and a description of the way that we present them in this text.
1.1 Organic Molecules
All organic molecules contain carbon (C), virtually all of them contain hydrogen (H), and
most contain oxygen (O) and/or nitrogen (N) atoms. Many organic molecules also have
halogen atoms such as fluorine (F), chlorine (Cl), bromine (Br), or iodine (I). Other atoms in
organic compounds include sulfur (S), phosphorous (P), and even boron (B), aluminum (Al),
and magnesium (Mg).
The number of different types of atoms in organic compounds suggests they are structurally
complex. Fortunately, we find these atoms in a relatively few specific arrangements because
of their preferred bonding characteristics. For example, C atoms primarily bond to each
other to form the molecular skeleton or backbone of organic molecules, while H atoms
bond to the various C atoms, or to other atoms such as N and O, almost like a "skin"
surrounding the molecule. You can see some of these features in the organic molecule lauric
acid that is one of a group of molecules called fatty acids. [graphic 1.1] Since atoms such as
N, O, and the halogens (generally referred to as X) connect to the carbon skeleton in
characteristic ways that determine the properties of a molecule, we call these groups of atoms
functional groups. Functional groups define the class to which the organic molecule
belongs.
Bonding Characteristics of Atoms (1.1A)
You can see that most of the atoms that we have mentioned above are in the first three rows
of the periodic table. [graphic 1.2] However, it is their location in a particular column of
the periodic table that tells us how many chemical bonds they usually form to other atoms in
a molecule. For example, C and Si are in the fourth column (Group 4A) and they each
typically have four bonds in their molecules, while F, Cl, Br, and I are in Column 7A and
they typically form just one bond.
Periodic Tables. The partial periodic table shown here does not include columns with the "transition
elements" (Groups 1B through 8B). We show these in the full periodic table located inside the cover
of your text. Some of these transition elements are present in organic molecules, but to a much smaller
extent than the other atoms we have mentioned. We will consider bonding preferences of transition
elements as needed throughout the text.
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